any semi-new bike is a theft magnet. Reliability is primarily a function of your awareness that things are adjusted right and fix them before they get out of hand or forced. $1000 max leaves out Cross-Check or LHT. Nearly flat proof tires are possible but they're heavy and you'll still need to keep them inflated.
Rear rack, room for fenders. $.02 whatever you get get a bunch of rolls of black cloth tape and wrap the top tube, seat post and seat stays then take a couple cans of clashing paint and go over the entire bike. You might consider turning the front crankset into a double if it's a triple with outer chainring taken up with chainguard to reduce tearing up friends cars when taken apart and stuffed into back seats/trunk. Pit-lock qr or seat post might be an idea.
Given your budget get this then pre-trash it.
http://www.bikesdirect.com/products/..._cross_cx3.htm